title: Diversification of a β-Lactam Pharmacophore via Allylic C-H Amination: Accelerating Effect of Lewis Acid Co-Catalyst.
abstract: This report describes the use of Pd(II)/bis-sulfoxide 1 catalyzed intra- and intermolecular allylic C-H amination reactions to rapidly diversify structures containing a sensitive β-lactam core similar to that found in the monobactam antibiotic Aztreonam. Pharmacologically interesting oxazolidinone, oxazinanone, and linear amine motifs are rapidly installed with predictable and high selectivities under conditions that use limiting amounts of substrate. Additionally, we demonstrate for the first time that intramolecular C-H amination processes may be accelerated using catalytic amounts of a Lewis acid co-catalyst [Cr(III)(salen)Cl 2].
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801 USA.
authors.forename: Xiangbing Ben
authors.initials: XB
authors.lastname: Qi
authors.forename: Grant T
authors.initials: GT
authors.lastname: Rice
authors.forename: Manjinder S
authors.initials: MS
authors.lastname: Lall
authors.forename: Mark S
authors.initials: MS
authors.lastname: Plummer
authors.forename: M Christina
authors.initials: MC
authors.lastname: White